Sahil Bloom Profile picture
Feb 6 26 tweets 5 min read
It’s Sunday evening, freezing outside, and I’m yet again two whiskeys deep…

A few hot takes and semi-coherent thoughts:
Being INTERESTED is more important than being INTERESTING.

Interested people are prone to giving their deep attention to something to learn more about it.

They ask questions, listen, and observe. They open up to the world around them.

The interested inevitably win.
Every team needs more tugboats.

Tugboats are my favorite. Small, unassuming, and often quite ugly—but capable of pulling massive ships.

Tugboats are the 10X hires at your startup or business.

They aren’t the sexy hire (the yacht)—but they are infinitely more valuable.
If you want to get lucky, start by increasing your luck surface area.

It’s hard to get lucky watching TV at home.

It’s (relatively) easy to get lucky when you’re engaging with people, interacting, and learning—physically or digitally.

Put yourself in a position to get lucky.
Networking is dead.

You don’t get anywhere in life by accumulating thousands of loose, transactional connections. It’s a transparent race to the bottom.

You get somewhere by building genuine relationships—by helping people with no end in mind.

Stop networking, start building.
We really need to normalize boredom.

Some of your most creative moments come during periods of boredom.

In the shower, on a walk, at a dinner by yourself.

You’re bored, your mind wanders, your thoughts mingle. Bam! Creative insight strikes.

Normalize periods of boredom.
Stop trying to be all things to all people.

My life got 10X better when I got comfortable being myself and stopped worrying about getting everyone to like me.

Do you. Some people will like it, some people wont—that’s ok.

Just do you.
Polygamous work is the future.

Old Way: Graduate, take a job, work for 40 years, get a gold watch, retire.

New Way: Work in a variety of roles that keep your whole self fulfilled.

The infrastructure to enable this shift is going to be fascinating to watch (and invest in).
Everyone should eat dinner alone at a bar or restaurant at least once per month.

In school, we were taught that eating alone was the worst thing imaginable—a sign of being a social outcast.

In adulthood, I’d argue it’s the opposite—a sign of being free.

Try it. Thank me later.
Passion is overrated—or at least an unnecessary limiting factor.

I’ve become passionate about things the more I learned about them.

If I refused to dive in on something because I didn’t feel passion already, I’d never go deeper on anything.

You should strive to be an explorer.
Stop blaming time and giving your focus a free pass.

I often find myself complaining that I don’t have time to get to various high-priority projects.

Then I do an honest assessment and realize time wasn’t to blame—my focus was.

Put your focus on notice—force it to level up.
Imposter syndrome is a good thing most of the time.

Everyone writes fighting imposter syndrome, but I think we should just embrace it.

We feel like imposters because we are imposters—and that’s totally ok.

Everyone’s an imposter until they aren’t. Let it motivate you to grow.
Everyone should carry a pocket notebook—and nice pen—with them at all times.

It gives you a medium to document miscellaneous daily learnings that is completely disconnected from technology.

It’s also a more polite—and sneaky swaggy—way to take notes when meeting someone new.
Written memos are 100x more useful than beautiful slide decks.

Slides are useful for:
• Ted Talks
• PTA Meetings
• Keeping shredders busy

Memos tell you more about how a person thinks, provide depth of insight, and lead to productive meetings.

Normalize written memos!
There’s no shortage of great ideas and opportunities, just a shortage of people willing to put in the effort to capitalize on them.

Ideas are cheap, execution is expensive.

The best way to stand out from the crowd is to be a doer.

Talkers talk. Builders build.
Life gets so much better once you realize you can learn from literally anyone.

No one is too old, young, rich, poor, etc. to teach you something new.

I’ve learned way more from a conversation with my Uber driver than on a zoom call with some famous Twitter gurus.
Way more people should become students of history.

The smartest and most successful people I know share one trait in common—they are all history buffs.

Why?

History may not repeat itself, but humans definitely do.
If your smart friends are talking about something that sounds crazy to you, you should pay attention.

I’ve ignored this signal on two occasions:
• Bitcoin (2013)
• NFTs (BAYC)

Both cost me a lot of money.

I’ll never make that mistake again, and I suggest you don’t either.
The sunk cost fallacy is the biggest driver of wasted potential.

So many people stay in careers they aren’t cut out for because of the sunk cost fallacy—they think that the foundational years will be a waste if they make a change.

You get one shot. View your career objectively.
Build something sexy for show, but something boring for dough.

Entrepreneurs obsess over building something complex and highly interesting, but that’s where all the competition is. It’s fierce.

Build something complex and boring if you want to optimize for creating real wealth.
Ok…that’s all for now. I’m now three whiskeys deep and I have a steak calling my name.

Follow me @SahilBloom for more—hopefully semi-coherent—thoughts in the future.

Much love!
I’m taking a bunch of shit from friends and @ParikPatelCFA for being a lightweight…

I don’t eat until dinner on Sundays. You try drinking two whiskeys on an empty stomach and remaining sober. Good luck.
And for everyone asking, here was the whiskey of choice this evening:

Kentucky Owl 10-Year Rye

Oaky, nutty—really, really good.
By the way, I’m not saying any of these takes are *correct* or *definitively true*—just my off-the-cuff perspectives on a variety of topics.

I welcome disagreements. I’m always ready and willing to change my mind on things when presented with good faith counterarguments.
And here was last week’s Whiskey Ramblings for anyone interested in going deeper down the rabbit hole…
It’s Monday morning, I have a (mild) hangover, and I’m two large @dunkindonuts cold brews deep.

My mom texted me telling me to stop drinking so much. Sorry, Mom—I think I have to take one for the team and keep it rolling.

🤯🥃

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More from @SahilBloom

Feb 8
I think there are multiple $1B+ business opportunities in providing financial services specifically catered to non-W2 employees.

Here’s my rationale and vision:
In traditional financial services, W2 income reigns supreme.

As a bit of history, the use of the Form W-2 was first established by the Current Tax Payment Act of 1943 as part of an effort to withhold income at the source.

The first Form W-2s were issued to employees in 1944.
The W-2 became the primary source of truth for information about an employee's income.

Financial services infrastructure was built around this source of truth.

In particular, loan underwriting—for mortgages or personal loans—became heavily reliant on stable, growing W2 income.
Read 11 tweets
Feb 5
How to stop procrastinating:
Confession: I spent most of my life as a chronic procrastinator.

I also spent most of my life justifying that chronic procrastination—both internally and externally.

I told myself it was "just how I worked”—that the pressure of an imminent deadline was what I needed to thrive.
To be fair, I wasn't wildly off:

The Yerkes-Dodson Law says pressure and performance are positively correlated—up to a point, after which more pressure reduces performance.

The real issue: procrastination meant I only worked on the urgent—very rarely the long-term important.
Read 23 tweets
Feb 4
I think there’s a $1,000,000 opportunity in creating a paid "Explain It To Me Like I'm 5" curation newsletter for tech, business, or marketing.

Here’s how I’d do it:
The problem: So much great content, so little time.

The solution: Weekly TLDR summary of best pieces of content from a given vertical.

• Tech
• Marketing
• Finance

It is critical that the summaries abstract the complexity and provide a simplified version of the original.
Economic model could look like:

Charge $20 per month.

50% of all gross proceeds go into a pool that is distributed back to the original content creators monthly to compensate them for their efforts.

Would need ~4,200 subs to do $1m gross, $500k net annually.

How I’d get them:
Read 10 tweets
Feb 4
“Either write something worth reading or do something worth writing.” - Benjamin Franklin

Stories have the power to change the world. Be a story-teller or be a story-creator.

Check out today’s Friday Five! Learn something interesting, every single week. sahilbloom.substack.com/p/the-friday-f…
Huge shoutout to @cleoabram and @Nathanbarry—two of my favorite new creator discoveries—both featured in this week’s episode.

Cleo’s new “Huge If True” is going to be huge. Would invest!
One addition to the Franklin quote that came from the community…

Read something worth learning.

I like that.
Read 4 tweets
Feb 3
If you want to start a business but you’re struggling to come up with a great idea...

Here’s a tactical approach for idea generation:
This approach leverages one of my favorite business frameworks:

Clayton Christensen’s Model of Disruptive Innovation

In simple terms, it says that innovators can win market share by serving a segment of the market that is over or underserved by the big incumbent’s offering.
Basically, upstarts can win market share by serving one sub-segment of a big market extremely well.

Provide the exact level of product/service needed and use it as a wedge to expand.

Ok, now let’s get tactical.

Here’s how you can use the framework to generate business ideas:
Read 14 tweets
Feb 3
Y Combinator has been in the news a lot lately...

In the latest episode of Where It Happens, Eight Sleep founder @m_franceschetti tells us the crazy story of being rejected from YC twice and how he finessed the system to win.

It was epic…

Listen: podcasts.apple.com/us/podcast/how…
Other links to listen or watch!

Spotify: open.spotify.com/episode/6wZDP3…

YouTube:
And join the conversation in our discord with 4,000+ others! discord.gg/P8EJhjk8
Read 4 tweets

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